Methanol → Cyclopropanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyridin-8-yl]-amide

HRID 1259421Notes

Reaction equation

HRID 1259421 reaction equation
[CH:1]1([S:4](Cl)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[NH2:8][C:9]1[C:14]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([I:22])=[CH:18][C:17]=2[F:23])=[C:13]([CH3:24])[C:12](=[O:25])[N:11]2[CH2:26][CH2:27][S:28][C:10]=12.CO>N1C=CC=CC=1.C(Cl)(Cl)Cl>[F:23][C:17]1[CH:18]=[C:19]([I:22])[CH:20]=[CH:21][C:16]=1[NH:15][C:14]1[C:9]([NH:8][S:4]([CH:1]2[CH2:3][CH2:2]2)(=[O:6])=[O:5])=[C:10]2[S:28][CH2:27][CH2:26][N:11]2[C:12](=[O:25])[C:13]=1[CH3:24]

Participants

6

Reactant 3

HCID 887MethanolHCID 2760919Cyclopropanesulfonyl chlorideHCID 583805858-Amino-7-(2-fluoro-4-iodo-phenylamino)-6-methyl-2,3-dihydro-thiazolo[3,2-a]pyridin-5-one

Product 1

HCID 52911938Cyclopropanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyridin-8-yl]-amideYield 22.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

Cyclopropane sulfonyl chloride (34 mg, 0.23 mmol) was added to a solution of 8-amino-7-(2-fluoro-4-iodo-phenylamino)-6-methyl-2,3-dihydro-thiazolo[3,2-a]pyridin-5-one (0.09 g, 0.21 mmol) in pyridine (1 mL) at 0° C. The resulting mixture was stirred at room temperature overnight. The reaction was monitored by TLC (5% MeOH in CHCl3). The reaction mixture was partitioned between ethylacetate and water. The organic layer was washed with 2N HCl, brine solution, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (1% MeOH in CHCl3), followed by preparative HPLC afforded 25 mg of the product (22% yield).

Workup

  1. customThe reaction mixture was partitioned between ethylacetate and water
  2. washThe organic layer was washed with 2N HCl, brine solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by column chromatography on silica gel (1% MeOH in CHCl3)

Sources & evidence

ORD record
ord-297a48e6fb6547b6a4a2e30d2d5ac306
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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